EP0809625B1 - Composes amphiphiles anioniques, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diamides d'acides dicarboxyliques - Google Patents

Composes amphiphiles anioniques, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diamides d'acides dicarboxyliques Download PDF

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Publication number
EP0809625B1
EP0809625B1 EP95940196A EP95940196A EP0809625B1 EP 0809625 B1 EP0809625 B1 EP 0809625B1 EP 95940196 A EP95940196 A EP 95940196A EP 95940196 A EP95940196 A EP 95940196A EP 0809625 B1 EP0809625 B1 EP 0809625B1
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formula
compounds according
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independently
compounds
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EP0809625A1 (fr
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Klaus Kwetkat
Herbert Koch
Wulf Ruback
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Sasol Germany GmbH
Wintershall Dea International AG
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RWE Dea AG fuer Mineraloel und Chemie
RWE Dea AG
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/22—Amides or hydrazides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/34—Derivatives of acids of phosphorus
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group

Definitions

  • the invention relates to amphiphilic compounds having at least two hydrophilic and at least two hydrophobic groups based on diamides.
  • a large variety of anionic, cationic, known nonionic and zwitterionic compounds consist of a hydrophilic head group and at least one hydrophobic part.
  • amphiphilic substances there are, for ecological reasons, z. B. regarding the reduction of packaging and transport costs, the necessity, always to achieve greater effect per mass of substance used.
  • z. B. regarding the reduction of packaging and transport costs, the necessity, always to achieve greater effect per mass of substance used.
  • New amphiphilic substances with a higher degree of effectiveness are required.
  • substances with lower critical micelle concentrations must therefore be used and / or lower surface and interfacial tensions are found, in order to be able to significantly reduce the amount of active substance used.
  • cationic surface-active compounds can be obtained by the addition of long-chain alkyl halides to permethylated alkylenediamines [R. Zana, M. Benrraou, R. Rueff, Langmuir, 7 (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].
  • Anionic surface-active compounds with at least two hydrophilic and at least two hydrophobic groups are so far only based on diglycidyl ethers (US 5 160 450, JP 01 304 033, JP 4 124 165).
  • Diglycidyl ether however, are considered toxicologically questionable and are quite expensive.
  • Epichlorohydrin is used for their production, resulting in large amounts of residual materials Leads, so that these compounds under ecotoxicological as well as economic Are no longer up to date.
  • the task was therefore to find amphiphilic compounds that have at least two hydrophilic and at least two hydrophobic groups, the amphiphilic compounds having a very high efficiency, based on the amount used, and those that are technically easily available Raw materials produced without a large amount of unwanted by-products can be.
  • amphiphilic diamides the basic structure of which can be prepared from dicarboxylic acids or their esters and amines.
  • the corresponding di- or oligoamides can be alkoxylated.
  • These nonionic amphiphilic compounds are converted into anionic amphiphilic compounds by z.
  • anionic amphiphilic compounds according to the invention are therefore compounds of the general formula I. where R 1 , R 2 , R 3 , X and Y in the formula I have the meanings described below:
  • R 1 and R 3 independently of one another represent an unbranched, saturated or unsaturated hydrocarbon radical having 1 to 22, preferably 7 to 17, carbon atoms.
  • the individual substituents R 1 and R 3 are methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n -Undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-henicosyl, n-docosyl and the corresponding simple , called double or triple unsaturated radicals.
  • the degree of alkoxylation is in each case an average value and can be any, including not take an integer value within the specified limits.
  • amphiphilic compounds according to the invention are usually characterized by extreme low critical micelle concentration (CMC) and very low surface and interfacial tension (e.g. against paraffin) from what on their particular Structure - at least two hydrophilic groups and at least two hydrophobic groups Groups - must be returned.
  • CMC critical micelle concentration
  • very low surface and interfacial tension e.g. against paraffin
  • most of them have of them have a fairly high hydrophilic suspension capacity, about half that Paths between conventional surfactants and pentasodium tripolyphosphate lies.
  • Some of these compounds are extremely fast wetting agents.
  • amphiphilic compounds according to this invention are particularly useful as Emulsifiers, demulsifiers, detergents, dispersants and hydrotropes in industry and household, for example in the fields of metalworking, ore mining, Surface finishing, washing and cleaning, cosmetics, medicine and food processing and preparation.
  • nonionic surfactants used for a combination can be mentioned: fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, Ethoxylates of higher alcohols, polyoxyethylene fatty acid glycerides, Polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene sorbitan fatty acid ester, Polyoxyethylene castor oil or hydrogenated castor oil derivatives, polyoxyethylene lanolin derivatives, Polyoxyethylene fatty acid amides, polyoxyethylene alkylamines, alkanolamines, Alkylamine oxides, derivatives of protein hydrolysates, hydroxy mixed ethers, alkyl polyglycosides and alkyl glucamides.
  • anionic surfactants suitable for combinations are: soaps, ether carboxylic acids and their Salts, alkyl sulfonates, ⁇ -olefin sulfonates, sulfonates of higher fatty acid esters, alcohol sulfates, Alcohol ether sulfates, hydroxy mixed ether sulfates, salts of phosphate esters, Taurides, isethionates, linear alkylbenzenesulfonates, cumene sulfonates, alkylarylsulfonates, Sulfates of polyoxyethylene fatty acid amides and salts of acylamino acids.
  • cationic surface-active substances commonly used for combinations can be used, may be mentioned: alkyltrimethylammonium salts, Dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, alkylpyridinium salts, Alkyl isoquinolinium salts, benzethonium chlorides and cationic acyl amino acid derivatives.
  • ampholytic surfactants suitable for combinations may be mentioned: amino acids, betaines, sulfobetaines, Imidazoline derivatives, soybean oil lipids and lecithin.
  • amphiphilic compounds according to the invention can also be used for can be combined with each other.
  • additives can also be used with the amphiphilic compounds according to the invention can be added.
  • Such additives are specially selected for a formulation and usually include inorganic salts such as sodium chloride and sulfate, and also builders, hydrotropes, UV absorbers, plasticizers, chelating agents, viscosity modifiers and fragrances.
  • the dicarboxylic acids or their methyl esters are with two equivalents of amine elevated temperatures (80 to 240 ° C) optimally in the presence of a catalyst reacted, the resulting water or methanol being removed under vacuum.
  • dicarboxylic acid-N, N'-dialkyldiamides they become at temperatures alkoxylated from 130 to 190 ° C under pressure in the presence of a basic catalyst.
  • this step is optional.
  • the products can then be reacted with SO 3 / inert gas (oleum, chlorosulfonic acid or amidosulfonic acid) or polyphosphoric acid or with a haloacetic acid, a sultone, with maleic anhydride and sodium hydrogen sulfite or with isethionic acid and neutralized with aqueous alkali metal or alkaline earth metal hydroxides or ammonia or alkanolamines.

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Claims (7)

  1. Composés amphiphiles anioniques de formule générale I
    Figure 00190001
       dans laquelle R1 et R3 représentent, indépendamment l'un de l'autre, un radical hydrocarboné linéaire, saturé ou insaturé comprenant 1 à 22 atomes de carbone
    R2 représente
       une chaíne alkylène linéaire ou ramifiée de formule II -CaH2a-    avec a = 2 à 18,
       une chaíne alcénylène linéaire ou ramifiée de formule III -CbH2b-CH=CH-CcH2c-    avec b + c = 2 à 16, b et c étant à chaque fois supérieurs à 0,
       une chaíne alcynylène linéaire ou ramifiée de formule IV -CdH2d-C≡C-CeH2e-    avec d + e = 2 à 16, d et e étant à chaque fois supérieurs à 0,
       des alicycles selon la formule V -CfH2f-cyclo C6H10-CgH2g-    avec f et g = chacun 1 à 6,
       ou selon la formule VI -3(4),8(9)-di(méthylène)tricyclo[5.2.1.02.6]décane-    des aromates non substitués ou substitués selon la formule VII -ChH2h-C6R4-(CiH2i-C6R4)j1-Cj2H2j2-    ou selon la formule VIII -ChH2h-C10R6-CjH2j-    avec h, j, j1 et j2 = chacun 0 à 8 et i = 1 à 8
       avec R = indépendamment l'un de l'autre à chaque fois H ou alkyle en C1 à C4,
       un groupement selon la formule IX -CkH2k-CxRy-Z-CxRy-ClH2l-    avec k et l = chacun 0 à 8, x = 6 et y = 4 ou
          x = 10 et y = 6 ou x = 14 et y = 8 et
          Z = O, CO, NH, NR1, N-C(O)R1, SO2, où R1 signifie un radical hydrocarboné comprenant 1 à 22 atomes de carbone et R signifie, indépendamment l'un de l'autre, à chaque fois H ou alkyle en C1 à C4,
          un groupement selon la formule X -CmH2m-(OCnH2n)p-CqH2q-       avec m = 1 à 4, n = 2 à 4, p = 1 à 20, de préférence p = 1 à 6, et q = 1 à 4,
          des unités mixtes alkoxyde pouvant également exister et l'ordre des unités alkoxyde étant quelconque,
          un groupement selon la formule XI -CrH2r(RNCsH2s)t-CuH2u-    ou selon la formule XII - [CrH2r[RN-C(O)-NR]t-CuH2u]w-       ou selon la formule XIII - [CrH2r[RNC(O)CvH2vC(O)NR]t-CuH2u]w-       ou selon la formule XIV - [CrH2r[RN-C(O)-CH=CH-C(O)-NR]t-CuH2u)w-       ou selon la formule XV - [CrH2r [RNC (O) CxRyC (O) NR]t-CuH2u]w-       avec r = 2 à 4, s = 2 à 4, t = 1 à 20, u = 2 à 4, v = 0 à 12, w = 1 à 6, x = 6 et y = 4 ou
          x = 10 et y = 6 ou
          x = 14 et y = 8
          avec R = indépendamment l'un de l'autre à chaque fois H ou alkyle en C1 à C4, et
    X ou Y représentent, indépendamment l'un de l'autre, un substituant de formule XVI - (C2H40)α(C3H60)βH       avec α = 0 à 50,
          β = 0 à 60,
          et a+β = 1 à 100,
          ou un substituant de formule XVII -(C2H4O)γ(C3H6O)δ-FR       avec à chaque fois γ = 0 à 20,
          δ = 0 à 20,
          γ+δ = 1 à 40,
          FR représentant un radical fonctionnel -CH2-COOM, -SO3M, -P(O)(OM)2, -O-C(O)-C2H3(SO3M)-CO2M' ou -C2H4SO3M, avec M, M' = alcali, ammonium, alcanolammonium ou 1/2 alcalino-terreux,
          ou un substituant de formule XVIII -CH2[CHO(C2H4Oε(C3H6O)ηA]z-CH2-O(C2H4O)µ(C3H6O)ρ-A       avec z = 3 à 6,
          et ε ou selon le cas µ = 0 à 30,
          et η ou selon le cas ρ = 0 à 30,
          et A représentant H ou FR,
          et, pour des alkoxydes mixtes, les unités alkoxyde étant insérées statistiquement ou en blocs et l'ordre étant quelconque.
  2. Composés selon la revendication 1, caractérisés en ce que l'espaceur R2 correspond à la formule II et contient 2 à 6 atomes de carbone.
  3. Utilisation des composés selon l'une quelconque des revendications 1 ou 2 comme émulsifiant ou désémulsifiant.
  4. Utilisation des composés selon l'une quelconque des revendications 1 ou 2 comme adjuvant lors du traitement de métaux, de l'extraction de minerais ou du finissage de surfaces.
  5. Utilisation des composés selon l'une quelconque des revendications 1 ou 2 comme adjuvant pour textiles ou pour le lavage et le nettoyage de textiles.
  6. Utilisation des composés selon l'une quelconque des revendications 1 ou 2 pour le nettoyage de surfaces dures.
  7. Utilisation des composés selon l'une quelconque des revendications 1 ou 2 pour le nettoyage et le lavage de la peau et des cheveux.
EP95940196A 1995-02-17 1995-11-17 Composes amphiphiles anioniques, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diamides d'acides dicarboxyliques Expired - Lifetime EP0809625B1 (fr)

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Application Number Priority Date Filing Date Title
DE19505368A DE19505368A1 (de) 1995-02-17 1995-02-17 Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediamiden
DE19505368 1995-02-17
PCT/EP1995/004530 WO1996025388A1 (fr) 1995-02-17 1995-11-17 Composes amphiphiles, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diamides d'acides dicarboxyliques

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EP0809625A1 EP0809625A1 (fr) 1997-12-03
EP0809625B1 true EP0809625B1 (fr) 2001-04-11

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US (1) US6121482A (fr)
EP (1) EP0809625B1 (fr)
JP (1) JPH11500715A (fr)
CN (1) CN1175243A (fr)
AT (1) ATE200480T1 (fr)
AU (1) AU4173196A (fr)
BR (1) BR9510316A (fr)
DE (2) DE19505368A1 (fr)
ES (1) ES2158958T3 (fr)
TR (1) TR199600111A2 (fr)
WO (1) WO1996025388A1 (fr)
ZA (1) ZA961229B (fr)

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DE4440328A1 (de) * 1994-11-11 1996-05-15 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Amiden
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DE19505368A1 (de) 1996-08-22
ES2158958T3 (es) 2001-09-16
CN1175243A (zh) 1998-03-04
ATE200480T1 (de) 2001-04-15
DE59509193D1 (de) 2001-05-17
US6121482A (en) 2000-09-19
EP0809625A1 (fr) 1997-12-03
BR9510316A (pt) 1997-11-11
WO1996025388A1 (fr) 1996-08-22
JPH11500715A (ja) 1999-01-19
TR199600111A2 (tr) 1996-10-21
AU4173196A (en) 1996-09-04

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